cis-1-(9-anthryl)-3-phenyl-1-propen-3-one | 87337-01-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: cis-1-(9-anthryl)-3-phenyl-1-propen-3-one
• 英文别名: (Z)-3-(9-anthryl)-1-phenylpropenone；cis-3-(9-anthryl)-1-phenyl-prop-2-en-1-one；3-anthracen-9-yl-1-phenyl-prop-2-enone；cis-APO；3-(anthracen-9-yl)-1-phenylprop-2-en-1-one；(Z)-3-anthracen-9-yl-1-phenylprop-2-en-1-one
• CAS: 87337-01-7
• 化学式: C₂₃H₁₆O
• 分子量: 308.379
• InChiKey: HTNKWVPCJOMMPQ-PFONDFGASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  cis-1-(9-anthryl)-3-phenyl-1-propen-3-one 生成 (E)-3-(anthracen-9-yl)-1-phenylprop-2-en-1-one
  参考文献：
  名称：

  将二元分子组分协同组装成管状结构，以用于多光子应用

  摘要：

  以管为例：管状结构可以通过二元分子组分TPI和APO的协同自组装来制造（见图）。该方法还可用于制造能够执行多种光子功能的单个二元管，例如环形微腔波导，波导调制和可控波导开关。

  DOI：

  10.1002/anie.201006681
• 作为产物：
  描述：

  (E)-3-(anthracen-9-yl)-1-phenylprop-2-en-1-one 生成 cis-1-(9-anthryl)-3-phenyl-1-propen-3-one
  参考文献：
  名称：

  将二元分子组分协同组装成管状结构，以用于多光子应用

  摘要：

  以管为例：管状结构可以通过二元分子组分TPI和APO的协同自组装来制造（见图）。该方法还可用于制造能够执行多种光子功能的单个二元管，例如环形微腔波导，波导调制和可控波导开关。

  DOI：

  10.1002/anie.201006681

文献信息

• Photochemistry of the anthracene chromophore: novel isomerization of 1-(9-anthryl)-2-benzoylethylenes
  作者：Hans-Dieter Beeker、Hans-Christian Becker、Kjell Sandros、Kjell Andersson

  DOI：10.1016/s0040-4039(00)98559-9

  日期：——

  Photoexcited cis-1-(9-anthryl)2-benzoylethylenes undergo a novel type of isomerization by skeletal rearrangement to give furano-annelated 5H-dibenzo[a,d]cycloheptenes.

  光激发的顺式-1-（9-蒽基）2-苯甲酰基乙烯通过骨架重排经历新型异构化反应，从而生成呋喃基退火的5H-二苯并[a，d]环庚烯。
• On the relationship between molecular geometry and excited-state properties of 9-anthrylalkenes
  作者：Hans Dieter Becker、Kjell Andersson

  DOI：10.1021/jo00172a020

  日期：1983.12
• Structures and photochemical reactions of 1-(9-anthryl)-2-aroylethylenes: competing <i>cis</i>–<i>trans</i> isomerization and skeletal rearrangement
  作者：Y. Mori、K. Maeda

  DOI：10.1107/s0108768193008961

  日期：1994.2.1

  (Z)-3-(9-Anthryl)-1-phenylpropenone, cis-(I), C23-H16O, M(r) = 308.38, orthorhombic, P2(1)2(1)2(1), a = 14.992 (3), b = 19.124 (4), c = 5.614 (1) angstrom, V = 1609.4 (6) angstrom3, Z = 4, D(x) = 1.273 g cm-3, mu = 0.071 mm-1, F(000) = 648, R = 0.061 for 1101 observed reflections; (Z)-2-(9-anthrylmethylene)-1-indanone, cis-(III), C24H16O, M(r) = 320.40, monoclinic, P2(1)/a, a = 11.641(5), b=13.914 (10), c = 10.399 (6) angstrom, beta = 102.71 (4)degrees, V = 1643.1 (16) angstrom3, Z = 4, D(x) = 1.295 g cm-3, a = 0.072 mm-1, F(000) = 672, R = 0.060 for 2321 observed reflections; (Z)-2-(9-anthrylmethylene)-1-tetralone, cis-(IV), C25H18O, M(r) = 334.39, monoclinic, P2(1)/c, a = 9.106 (4), b = 25.977 (9), c = 7.478 (2) angstrom, beta = 96.76 (5)degrees, V = 1756.6 (11) angstrom3, Z = 4 D(x) = 1.264 g cm-3, mu = 0.070 mm-1, F(000) = 704, R = 0.070 for 1594 observed reflections; (E)-2-(9-anthrylmethylene)-1-tetralone, trans-(IV), C25H18O, M(r) = 334.39, monoclinic, P2(1)/c, a = 12.032 (2), b = 13.608 (3), c = 10.829 (3) angstrom, beta = 95.78 (2)degrees, V = 1764.1 (7) angstrom3, Z = 4, D(x) = 1.259 g cm-3, mu = 0.070 mm-1, F(000) = 704, R = 0.055 for 1985 observed reflections. cis-(I), cis-(III) and cis-(IV) exist in a conformation similar to each other, in which the anthracene plane forms a large dihedral angle [75.5 (3), 64.5 (1) and 67.2 (2)degrees, respectively] with the ethylene plane. These compounds rapidly undergo photochemical cis-trans isomerization in solution, while irradiation of cis-(I) in the solid state almost exclusively afforded an intramolecular [4+2] cyclization product, suggesting that the isomerization would be inhibited by crystal-lattice constraints. cis-(IV) also underwent [4+2] cyclization in the solid state, while in the case of cis-(III) only cis-trans isomerization was observed both in solution and in the solid state. A comparison of the molecular structures of cis-(I), -(III) and -(IV) suggested that the C(6)...O distance, where a new bond would be formed in the cyclization process, should be related to the photochemical reactivity.
• BECKER, H. -D.;BECKER, H. -CH.;SANDROS, K.;ANDERSSON, K., TETRAHEDRON LETT., 1985, 26, N 12, 1589-1592
  作者：BECKER, H. -D.、BECKER, H. -CH.、SANDROS, K.、ANDERSSON, K.

  DOI：——

  日期：——